The Massachusetts Supreme Judicial Court Contravenes United States Supreme Court in Sylvain, Ruling Padilla Rights Apply Retroactively

On the morning of Sunday, April 15, 2007, a Boston police officer was patrolling the streets of Dorchester when he spotted Kempess Sylvain apparently engaged in a sexual act with a prostitute.[ref]Commonwealth v. Sylvain, 995 N.E.2d 760, 763 (Mass. 2013).[/ref] As the officer approached, he saw Sylvain take several small plastic baggies from his coat and place them into his mouth. A search of Sylvain revealed an additional baggie of crack cocaine. He was arrested and charged with possession of cocaine with intent to distribute and a drug violation in a school zone, as the incident occurred within 1000 feet of a childcare center.[ref]See id.; see also Mass. Gen. Laws Ann. ch. 94C, § 32A(a) (West 2013) (prohibiting distribution of class B narcotics); ch. 94C, § 32J (providing additional penalties for possessing, distributing, or trafficking narcotics within 300 feet of school).[/ref] Sylvain—a noncitizen lawfully residing in the United States—pled guilty to simple possession of cocaine and received a suspended sentence. As a result, Sylvain automatically became subject to deportation, as the narcotics offense to which he pled guilty was a removable offense under federal immigration law.[ref]See Sylvain, 995 N.E.2d at 762; see also 8 U.S.C. § 1227(a)(2)(B)(i) (2012) (making noncitizens subject to deportation if convicted on controlled substances charges). Sylvain’s conviction became final on October 2, 2007. See Sylvain, 995 N.E.2d at 763. At the time of his appeal, however, Sylvain had not yet been deported. See id. at 763 n.3.[/ref]
 
In 2010, the Supreme Court held in Padilla v. Kentucky that a defendant’s Sixth Amendment right to effective assistance of counsel includes the right to advice on whether pleading guilty carries the risk of deportation.[ref]Padilla v. Kentucky, 559 U.S. 356, 360 (2010).[/ref] In 2011, the Massachusetts Supreme Judicial Court (SJC) ruled in Commonwealth v. Clarke that Padilla applied retroactively to all guilty pleas obtained after April 1, 1997, the date on which Congress implemented the current immigration laws regarding deportation for criminal convictions.[ref]See Commonwealth v. Clarke, 949 N.E.2d 892, 895 (Mass. 2011); see also Illegal Immigration Reform and Immigrant Responsibility Act of 1996, Pub. L. No. 104-208, 110 Stat. 3009-546 (codified as amended in scattered sections of 8 and 18 U.S.C.) (increasing number of deportable offenses); Antiterrorism and Effective Death Penalty Act of 1996, Pub. L. 104-132, 110 Stat. 1214 (codified as amended in scattered sections of the U.S.C.); Padilla, 559 U.S. at 360-64 (describing sweeping changes to federal immigration laws in prior ninety years); Matthew A. Spahn, Comment, Padilla Retroactivity: A Critique of the Tenth Circuit’s Ruling that Padilla v. Kentucky Does Not Apply Retroactively to Cases on Collateral Review, 51 Washburn L.J. 767, 767-68 (2012) (discussing 1996 amendments to federal immigration laws).[/ref] Clarke opened the door for Sylvain to appeal his conviction and, in 2012, he did. Sylvain alleged that his lawyer failed to advise that he could be deported if he pled guilty and that he would not have done so had he been so informed.[ref]See Commonwealth v. Sylvain, 995 N.E.2d 760, 762, 773 (Mass. 2013). Sylvain’s lawyer submitted an affidavit in support of Sylvain’s motion to vacate his guilty plea representing that he or she was aware of Sylvain’s noncitizen status, but had advised Sylvain that his guilty plea was not likely to result in his deportation. See id. at 764.[/ref] While Sylvain’s appeal was pending, the Supreme Court decided Chaidez v. United States, which held that Padilla does not apply retroactively under federal law, effectively overruling the SJC’s decision in Clarke.[ref]Chaidez v. United States, 133 S. Ct. 1103, 1113 (2013).[/ref] Upon hearing Sylvain’s appeal, the SJC diverged from the Supreme Court and held that, as a matter of state law, Padilla applies retroactively under the Sixth Amendment and Article XII of the Massachusetts Declaration of Rights.[ref]See Sylvain, 995 N.E.2d at 762; see also Mass. Const. pt. 1, art. XII (providing criminal defendants right to assistance of counsel).[/ref]
 

Padilla Rights and the Question of Retroactivity

 
The Sixth Amendment entitles criminal defendants to effective assistance of counsel in defending the charges against them.[ref]See U.S. Const. amend. VI (providing defendants right to “Assistance of Counsel for his defence”); McMann v. Richardson, 397 U.S. 759, 771 (1970) (establishing criminal defendant’s right to effective assistance of counsel); see also Spahn, supra note 5, at 772-75 (reviewing Sixth Amendment right-to-effective-assistance jurisprudence).[/ref] If defendants fail to receive such assistance, they may seek post-conviction relief under the two-prong test set forth in Strickland v. Washington by proving that: their counsel’s representation fell below an objective standard of reasonableness, and they were prejudiced by their lawyer’s deficient performance such that the result of the proceeding most likely would have been different but for the lawyer’s errors.[ref]See Strickland v. Washington, 466 U.S. 668, 687 (1984) (setting standard for ineffective assistance claims). The Massachusetts analog to Strickland is Commonwealth v. Saferian. See 315 N.E.2d 878, 882-83 (Mass. 1974) (adopting two-prong test largely similar to that in Strickland).[/ref] Strickland set a general standard of reasonableness to be applied on a case-by-case basis rather than defining a specific manner in which defense attorneys must advise their clients in any given scenario.[ref]See Roe v. Flores-Ortega, 528 U.S. 470, 476 (2000) (characterizing Strickland test as “objective standard of reasonableness”). The Supreme Court first applied Strickland to an ineffective assistance of counsel claim in the context of an entry of a guilty plea in Hill v. Lockhart. See 474 U.S. 52, 58-59 (1985) (establishing standard for ineffective assistance claims in context of guilty pleas).[/ref] In Padilla, the Supreme Court interpreted the Sixth Amendment within this construct and held that failing to advise criminal defendants on whether pleading guilty would subject them to deportation amounts to constitutionally deficient representation, thereby satisfying the first prong of the Strickland test.[ref]See Padilla v. Kentucky, 559 U.S. 356, 360 (2010). The Padilla Court justified its decision by pointing to the increased number of deportable offenses under federal law, the severity of deportation as a consequence of a criminal conviction, and the growing national consensus that professional norms demand attorneys inform clients of any risk of deportation should they plead guilty. See id. at 360-69. The Court rejected the government’s position that Strickland should apply only in instances where counsel gives affirmative misadvice regarding the immigration consequences of a guilty plea, reasoning that such a holding would incentivize attorneys to remain silent on such matters. See id. at 370-71. The Padilla Court left unsettled the exact scope of a defense attorney’s duty to advise her clients on immigration matters related to a potential guilty plea. See generally César Cuauhtémoc García Hernández, Criminal Defense After Padilla v. Kentucky, 26 Geo. Immigr. L.J. 475 (2012) (suggesting attorneys must advise clients charged with controlled substance offenses conviction will result in deportation).[/ref] The Padilla Court did not, however, expressly address whether this interpretation of Sixth Amendment rights applied retroactively to defendants whose convictions had already become final.
 
A court ruling that relates to an issue of constitutional criminal procedure applies retroactively only if it relies upon preexisting law. Thus, if a decision announces a “new” rule, then it only applies prospectively and to cases that are on direct review at the time of the decision.[ref]See Teague v. Lane, 489 U.S. 288, 301-02, 310 (1989) (adopting new retroactivity standard); see also Whorton v. Bockting, 549 U.S. 406, 416 (2007) (explaining federal retroactivity framework).[/ref] The Supreme Court first articulated this framework in Teague v. Lane, establishing that a rule is new if it “breaks new ground or imposes a new obligation” on the government or “if the result was not dictated by precedent existing at the time the defendant’s conviction became final.”[ref]Teague, 489 U.S. at 301 (1989). Massachusetts adopted the Teague standard in Commonwealth v. Bray. See 553 N.E.2d 538, 540-41 (Mass. 1990) (implicitly adopting Teague framework).[/ref] In later cases, the Supreme Court clarified that a result is “dictated by precedent” only if it would have been “apparent to all reasonable jurists” at the time of the decision.[ref]Lambrix v. Singletary, 520 U.S. 518, 527-28 (1997); see Williams v. Taylor, 529 U.S. 362, 410 (2000) (quoting Wright v. West, 505 U.S. 277, 304 (1992) (O’Connor, J., concurring)) (qualifying Lambrix by noting “mere existence of conflicting authority does not necessarily” make rule new).[/ref] In other words, a case does not announce a new rule under Teague if it merely applies an already existing principle to a new factual context.[ref]See Wright v. West, 505 U.S. 277, 308-09 (1992) (O’Connor, J., concurring) (noting principles of general application will rarely yield new rule).[/ref] In 2008, the Supreme Court decided in Danforth v. Minnesota that Teague sets a floor for the retroactive effect of rulings on criminal procedure rather than a ceiling.[ref]Danforth v. Minnesota, 552 U.S. 264, 279-82 (2008) (allowing states to provide broader retroactive effect than available under Teague).[/ref] Under Danforth, states reviewing their own criminal convictions are free to adopt their own standards for retroactivity and give broader retroactive effect to court rulings on criminal procedures than would otherwise be available under Teague.[ref]See id.; see also Jaclyn Kelley, Note, To Plea or Not To Plea: Retroactive Availability of Padilla v. Kentucky to Noncitizen Defendants on State Postconviction Review, 18 Mich. J. Race & L. 213, 227-29 (2012) (explaining Danforth); Jeffrey L. Fisher & Kendall Turner, The Retroactivity of Padilla After Chaidez v. United States, Champion, Mar. 2013, at 43, 44 & n.20 (highlighting Florida, Maryland, and Michigan’s adoption retroactivity standards different than Teague).[/ref] Indeed, states define crimes, punishments, and procedural rules in a variety of ways; thus, as long as those rules do not violate the U.S. Constitution, they are not limited by an abstract federal interest in uniformity.
 
In the wake of Padilla, state and federal courts quickly diverged on the question of whether the Supreme Court’s holding constituted a new rule under Teague and applied retroactively.[ref]See Spahn, supra note 5, at 784-85 (outlining split among state and federal courts over retroactivity of Padilla); Alison Syré, Note, Padilla v. Kentucky: Bending Over Backward for Fairness in Noncitizen Criminal Proceedings, 20 J.L. & Pol’y 677, 689-95 (2012). While a majority of state courts and federal district courts on the whole decided that Padilla applied retroactively, a majority of the federal circuit courts that have addressed the issue have concluded the opposite. See Spahn, supra note 5, at 784. Compare United States v. Orocio, 645 F.3d 630, 641 (3d Cir. 2011) (holding Padilla retroactive), with United States v. Amer, 681 F.3d 211, 214 (5th Cir. 2012) (holding Padilla not retroactive), United States v. Chang Hong, 671 F.3d 1147, 1158 (10th Cir. 2011), and Chaidez v. United States, 655 F.3d 684, 692-93 (7th Cir. 2011), aff’d, 133 S. Ct. 1103 (2013).[/ref] In Clarke, the SJC became the first state supreme court to interpret Padilla as having retroactive effect.[ref]See Commonwealth v. Clarke, 949 N.E.2d 892, 895 (Mass. 2011); see also Jesse M. Boodoo, Commonwealth v. Clarke: Padilla Ruled Retroactive in Massachusetts, Bos. B.J., Winter 2012, at 14, 14, available at http://www.bostonbar.org/pub/bbj/bbj_online/bbj1112/winter2012/CaseFocus.pdf (crediting SJC as first state supreme court to hold Padilla retroactive).[/ref] Applying the Teague framework, the SJC held that the Supreme Court had not announced a new rule in Padilla, but merely applied the well-established Strickland standard to a new type of ineffective assistance claim.[ref]Clarke, 949 N.E.2d at 899-902. In Clarke, the SJC also laid out the standard for proving the prejudice prong of the Strickland test in the context of a guilty plea, adopting the Supreme Court’s standard in Hill v. Lockhart. See id. at 905-06 (quoting Hill v. Lockhart, 474 U.S. 52, 59 (1985)).[/ref] The SJC relied on the Supreme Court’s own characterization of Strickland as a general standard that “provides sufficient guidance for resolving virtually all ineffective-assistance-of-counsel claims.”[ref]See id. at 900 (quoting Williams v. Taylor, 529 U.S. 362, 391 (2000)).[/ref] In February of 2013, however, the Supreme Court held in Chaidez that Padilla did announce a new rule of criminal procedure, which therefore did not apply retroactively. The Chaidez Court pointed to the fact that, prior to Padilla, state and federal courts almost unanimously agreed that criminal defense attorneys were not required to advise clients of the immigration consequences of pleading guilty. The Court therefore reasoned that the result in Padilla was not “apparent to all reasonable jurists” prior to the decision.[ref]Chaidez v. United States, 133 S. Ct. 1103, 1109, 1111 (2013) (7-2 decision) (noting ten circuit courts unanimously concluded Sixth Amendment did not require advice on deportation). The Chaidez Court also reasoned that Padilla announced a new rule because it concluded for the first time that “collateral consequences” of a criminal conviction, such as advice regarding deportation, can fall within the scope of the Sixth Amendment right to effective counsel. See id. at 1108, 1110. Chaidez was the first instance in which the Supreme Court upheld a claim for ineffective assistance of counsel under Strickland, but concluded that its holding did not apply retroactively. See id. at 1114-15 (Sotomayor, J., dissenting) (characterizing Padilla’s first application of Strickland to create new rule); Spahn, supra note 5, at 781-84 (reviewing history of retroactivity of Strickland claims).[/ref]
 

Massachusetts Splits From the Supreme Court in Sylvain

 
In Commonwealth v. Sylvain, the SJC rejected Chaidez and reaffirmed its holding in Clarke, ruling that Padilla did not announce a new rule and therefore applies retroactively to those convicted in Massachusetts after April 1, 1997.[ref]See Commonwealth v. Sylvain, 995 N.E.2d 760, 762 (2013); Clarke, 949 N.E.2d at 904 (holding Padilla applies retroactively).[/ref] Additionally, for the first time the SJC expressly announced that Article XII of the Massachusetts Declaration of Rights imposes the same obligation to advise defendants of the potential immigration consequences of pleading guilty as the Sixth Amendment does, and that a defendant’s right to such consultation also applies retroactively.[ref]See Sylvain, 995 N.E.2d at 771-72; see also Mass. Const. pt. 1, art. XII (providing right to assistance of counsel); Commonwealth v. Marinho, 981 N.E.2d 648, 656-57 (Mass. 2013) (implying Padilla applies retroactively under both the Sixth Amendment and Article XII).[/ref] Applying Massachusetts’ equivalent of the Strickland standard to Sylvain’s ineffective assistance claim, the SJC decided that his counsel’s representation was constitutionally inadequate, but remanded the case for further findings on whether Sylvain would have actually proceeded to trial had his lawyer properly informed him of the consequences of pleading guilty.[ref]See Sylvain, 995 N.E.2d at 773; see also supra note 10 (explaining Massachusetts adopted test largely similar to Strickland in Saferian).[/ref]
 
The SJC arrived at its conclusion by exercising its authority under Danforth to define its own standard—independent of that used by the Supreme Court in Chaidez—to evaluate the retroactive effect of Padilla. After surveying the Supreme Court’s retroactivity jurisprudence, the SJC characterized Teague and its progeny as establishing different definitions for what constitutes a new rule. The SJC rejected the “apparent to all reasonable jurists” standard and adopted what it characterized as the “original” Teague standard—that is, a case announces a new rule only when precedent does not dictate the result.[ref] See Sylvain, 995 N.E.2d at 769 (reconstituting Massachusetts’ retroactivity standard under Bray); see also supra note 14 (explaining Bray).[/ref] Under this narrowed retroactivity framework, the SJC reached the same conclusion as it did in Clarke for the same reasons: Padilla did not announce a new rule because Strickland dictated the result. The SJC asserted that Strickland is a general standard intended to evolve with prevailing professional norms and that Padilla was simply the Supreme Court’s recognition that professional norms now demand that defense counsel advise their clients on the immigration consequences of pleading guilty.
 

Retroactivity in the Realm of Criminal Law: Finality Versus Fairness

 
The question of whether to give convicted criminals additional constitutional rights by applying them retroactively poses a conflict between the fundamental values of ensuring the finality of criminal convictions and treating similar defendants the same. Our criminal justice system is premised on the idea that all convictions are final not only to protect the integrity of jury trials, but also to avoid draining the government’s resources by forcing it to continually relitigate cases.[ref]See Teague v. Lane, 489 U.S. 288, 309-10 (1989) (noting cost of relitigating cases). But see Kelley, supra note 14, at 235-37 (arguing finality considerations subordinate to fairness considerations in context of Padilla). See generally Richard H. Fallon, Jr. & Daniel J. Meltzer, New Law, Non-Retroactivity, and Constitutional Remedies, 104 Harv. L. Rev. 1731 (1991) (analyzing “new” law doctrines as constitutional remedies).[/ref] Some courts have warned that applying Padilla retroactively would open the floodgates to an overwhelming number of appeals by noncitizen convicts, creating an unmanageable administrative burden for courts.[ref]See United States v. Chang Hong, 671 F.3d 1147, 1159 (10th Cir. 2011) (expressing concern for protecting finality of judgments).[/ref] Moreover, allowing for the retrying of cases from years ago creates the potential for factually guilty defendants to go unpunished because the government is unable prove its case again without the same witnesses available.
 
On the other hand, considerations of fairness and justice are nowhere higher than when individual liberty and constitutional rights are at stake. Deciding that a criminal defendant on one day is entitled to certain legal advice, but a day earlier would not have been entitled to that same advice, seems unacceptably arbitrary given that such advice may be the difference between remaining in the United States and being deported. Such a result seems even less fair considering that deportation may, in many instances, be a grossly disproportionate punishment for the crime charged.[ref]See State v. Ramirez, 278 P.3d 569, 570 (N.M. Ct. App. 2012) (arguing deportation disproportionately severe punishment for relatively minor offenses).[/ref] Additionally, Strickland remains a high standard that any noncitizen hoping to challenge their conviction under Padilla must still hurdle, which may mitigate the number of frivolous Padilla appeals and the possibility of guilty defendants going free.
 
In Sylvain, the SJC decided that the concerns over fairness demanded that Padilla rights be made available to all defendants convicted under the current federal deportation laws and outweighed the potential costs of relitigating convictions. In Massachusetts, the most obvious consequence of Sylvain is that noncitizen defendants who pled guilty during the fourteen years before Padilla may now bring ineffective assistance claims if their lawyer did not advise them on the immigration consequences of pleading guilty. Although, as the SJC noted, it was already the norm in Massachusetts to advise defendants on the immigration consequences of pleading guilty, Sylvain reaffirms for the defense bar that the deportation warning given during a plea colloquy does not sufficiently alert defendants to the risks of pleading guilty.[ref]Commonwealth v. Sylvain, 995 N.E.2d 760, 763 n.2 (2013) (citing Commonwealth v. Clarke, 949 N.E.2d 892, 907 n.20 (Mass. 2011)) (explaining possibility of deportation in plea colloquy does not replace advice from counsel).[/ref] Thus, defendants may utilize Padilla on both Sixth Amendment and Article XII grounds. A less obvious consequence of Sylvain is that Massachusetts now has a new, albeit largely similar, retroactivity standard under which the SJC will analyze all future rulings on constitutional matters of criminal procedure.[ref]See supra note 27 and accompanying text (discussing reconstitution of retroactivity standards under Bray).[/ref]
 
If nothing else, Sylvain demonstrates the unique balance between state and federal law that defines the United States’ federal system. Massachusetts is the first state to sidestep Chaidez and apply Padilla retroactively as a matter of state law, as the six other state supreme courts to face this issue have all affirmed Chaidez.[ref]Compare Sylvain, 995 N.E.2d at 762 (holding Padilla retroactive), with Nguyen v. State, No. 11-0549, 2013 WL 1170326, at *2 (Iowa Mar. 22, 2013) (holding Padilla not retroactive), People v. Acosta, 831 N.W.2d 456, 456-57 (Mich. 2013) (denying application after Chaidez), State v. Osorio, 837 N.W.2d 66, 69-70 (Neb. 2013) (holding defendant cannot benefit from Padilla), Reyes v. State, No. 60363, 2013 WL 1093059, at *1 (Nev. Mar. 14, 2013) (holding Chaidez precludes defendant from benefiting from Padilla’s “new rule”), State v. Garcia, 834 N.W.2d 821, 826 (S.D. 2013) (declining to apply Padilla retroactively), and Ex Parte De los Reyes, 392 S.W.3d 675, 679 (Tex. Crim. App. 2013) (holding Padilla is not retroactive, but recognizing court could have held it is under Danforth). Although the Texas Court of Criminal Appeals technically is not the state’s supreme court, it is the final arbiter of all criminal appeals in Texas other than those in juvenile cases. See Court Structure of Texas, Tex. Courts Online (Sept. 1, 2013), http://www.courts.state.tx.us/pubs/JudicialDirectory/Court_Structure_Chart.pdf.[/ref] States that have yet to decide the issue may look to Massachusetts, as a case study, on whether the floodgates open and how many constitutionally infirm pleas are remedied that otherwise would not have been. Sylvain could serve as a beacon that leads other states to exercise their authority under Danforth to define their own retroactivity standards and apply Padilla retroactively; particularly in those states that declared Padilla retroactive prior to Chaidez. If Sylvain remains an outlier, it will nevertheless continue to serve as an important reminder of the distinction between the existence of a constitutional right and its procedural availability.